Personalization Evaluator - U.S. Small Business Owners (Google Workspace)

About the role

Our client is seeking U.S.-based small business owners to evaluate how well AI systems use information from connected Google Workspace applications to produce accurate, useful, and personalized responses. This is a hands-on evaluation role for people who understand real small business operations and use Gmail and Google Workspace extensively in their daily work.

What You'll Do

• Create realistic business-related prompts based on defined user goals.
• Interact with AI chatbots in conversations of up to five turns.
• Evaluate responses for accuracy, relevance, clarity, completeness, personalization, and usefulness.
• Assess how effectively the system retrieves context across Gmail, Chat, Calendar, Drive, Docs, Sheets, Slides, Meet, and other Workspace services.
• Identify missing, incorrect, or irrelevant context.
• Provide clear comparative ratings, structured feedback, conversation transcripts, and evaluation results.
• Follow project guidelines and maintain confidentiality and data privacy.

Who Should Apply

• You currently own or operate a small business with more than 10 employees.
• You have at least 2 years of relevant professional experience and strong knowledge of small business operations.
• Gmail is your primary business communication tool.
• You actively use multiple Google Workspace products, with especially heavy use of Chat, Drive, and Calendar.
• You have strong analytical and critical-thinking skills, can follow structured evaluation guidelines, and are comfortable working with AI tools.
• You are authorized to use any relevant business-account context involved in the project.
• Your resume includes a phone number and LinkedIn profile URL.

Engagement Details

• Remote contractor role for candidates in client-approved U.S. regions.
• Expected immediate start.
• 20-week engagement.
• 40 hours per week.
• At least 4 hours of overlap with Pacific Time.

Compensation

$42 per hour.